Here’s an ugly truth: If upgrades are hard, sysadmins try their best to avoid them. And that can cause security problems. Operating system upgrades can cause software that has worked well for years to develop nervous tics or stop working altogether. Fixing add-on packages that don’t work on the new operating system version can require days of troubleshooting. Server upgrades can make even seasoned sysadmins wish that they had a simpler job, such as performing as a carnival sideshow, stuffing weasels into their trousers.

While you can probably deal with a bit of odd behavior in a desktop after an upgrade, your servers and firewalls must behave exactly as expected. It’s common to delay upgrades until the system is so old that it can be replaced with a new machine running the new release, but that’s both terrible system administration practice and completely unacceptable security practice. Computers connected to the Internet must be patched, maintained, and upgraded, or an intruder will almost certainly compromise them.

Fortunately, the OpenBSD upgrade process is simpler than those used by many other Unix-like operating systems. With proper preparation, you can upgrade OpenBSD with a minimum of difficulty.